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Synthesis 2003(9): 1398-1402
DOI: 10.1055/s-2003-40188
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Generation of Pyridinium Ylides from N-(Silylmethyl)pyridone Analogs via 1,4-Silatropy and their 1,3-Dipolar Cycloadditions Leading to N-Heteropolycycles

Mitsuo Komatsu*, Yukihiro Kasano, Seiji Yamaoka, Satoshi Minakata
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Fax: +81(6)6879 7402; e-Mail: komatsu@ap.chem.eng.osaka-u.ac.jp;
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Publication History

Received 29 April 2003
Publication Date:
24 June 2003 (online)

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Abstract

Non-stabilized pyridinium methylides were successfully generated from N-(siliymethyl)pyridone analogs via 1,4-silatropy and the resulting 1,3-dipoles were trapped by reaction with acetylenic and olefinic dipolarophiles to afford N-heteropolycycles. The method does not require the use of any additives or strong bases.

Key words

1,3-dipolar cycloaddition - 1,4-silatropy - pyridinium methylides - pyridone analogs - N-heterocycles